4-Toluenesulfonyl chloride → HCID 24805800、化合物

HRID 905981ノート

反応式

HRID 905981 の反応式
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[F:12][C:13]([F:20])([F:19])[C:14]1([CH2:17][OH:18])[CH2:16][CH2:15]1.C(N(CC)CC)C>CN(C1C=CN=CC=1)C.C(Cl)Cl>[F:12][C:13]([F:20])([F:19])[C:14]1([CH2:17][O:18][S:7]([C:4]2[CH:5]=[CH:6][C:1]([CH3:11])=[CH:2][CH:3]=2)(=[O:9])=[O:8])[CH2:16][CH2:15]1

参加物

6

反応物 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 509906611-(Trifluoromethyl)cyclopropanemethanol

生成物 1

HCID 24805800HCID 24805800、化合物収率 49.4%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒

実験手順

p-Toluenesulfonyl chloride (9.6 g, 50.35 mmol) was added at 0° C. to a mixture of (1-trifluoromethyl-cyclopropyl)-methanol (7 g, 49.96 mmol), triethylamine (7.7 mL, 55.24 mmol) and DMAP (0.61 g, 4.996 mmol) in 100 mL of DCM. The resulting mixture was stirred at 0° C. to RT overnight before being washed with aqueous 1M HCl. The aqueous layer was back extracted twice with DCM. The combined organic layers were dried (Na2SO4), filtered, and evaporated. The residue was purified by SiO2 flash chromatography (120 g SiO2, hexanes/[hexanes/Et2O 8/2] 100 to 0% hexanes) to give 7.26 g of toluene-4-sulfonic acid 1-trifluoromethyl-cyclopropylmethyl ester (49% yield).

後処理

  1. washbefore being washed with aqueous 1M HCl
  2. extractionThe aqueous layer was back extracted twice with DCM
  3. dry with materialThe combined organic layers were dried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by SiO2 flash chromatography (120 g SiO2, hexanes/[hexanes/Et2O 8/2] 100 to 0% hexanes)

出典と根拠

ORDレコード
ord-350414da83904f549d161c385da9a23a
出典データセット
uspto-grants-2011_09
特許番号
US08012974B2

反応ノート

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